Crystal structure of bis-(4-allyl-2-meth-oxy-phen-yl) terephthalate.

The asymmetric unit of the title compound, C28H26O6, contains one half-mol-ecule, with the complete molecule generated by a crystallographic inversion center. The central terephthalate and meth-oxy-benzene rings are approximately perpendicular, making a dihedral angle of 80.31 (5)°. No specific directional contacts are noted in the crystal packing. The terminal vinyl group is disordered over two orientations with an occupancy ratio of 0.796 (4):0.204 (4).

Related literature

For general background to tyrosinase, see: Ha et al. (2007 ▶). For the development of tyrosinase inhibitors, see: Battaini et al. (2000 ▶); Thanigaimalai et al. (2010 ▶); Cabanes et al. (1994 ▶). For the structures of related compounds, see: Choi et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C28H26O6

M = 458.49

Triclinic,

a = 7.8853 (2) Å

b = 9.0404 (3) Å

c = 9.4801 (3) Å

α = 70.660 (4)°

β = 73.817 (3)°

γ = 75.145 (2)°

V = 602.28 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.15 × 0.14 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

21083 measured reflections

3008 independent reflections

1909 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.173

S = 1.09

3008 reflections

161 parameters

H-atom parameters not refined

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814021229/tk5342sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814021229/tk5342Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814021229/tk5342Isup3.cml

Click here for additional data file.

x y z . DOI: 10.1107/S1600536814021229/tk5342fig1.tif

Mol­ecular structure of the title compound, showing the atom-numbering scheme and 30% probability ellipsoids. Only major components of the disordered vinyl group are shown. Unlabeled atoms are related by −x, −y, 1-z]

CCDC reference: 1025706

Additional supporting information: crystallographic information; 3D view; checkCIF report

C28H26O6	Z = 1
Mr = 458.49	F(000) = 242
Triclinic, P1	Dx = 1.264 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8853 (2) Å	Cell parameters from 5115 reflections
b = 9.0404 (3) Å	θ = 2.3–26.7°
c = 9.4801 (3) Å	µ = 0.09 mm−1
α = 70.660 (4)°	T = 296 K
β = 73.817 (3)°	Block, colourless
γ = 75.145 (2)°	0.15 × 0.14 × 0.12 mm
V = 602.28 (4) Å3

Bruker SMART CCD area-detector diffractometer	Rint = 0.050
Radiation source: fine-focus sealed tube	θmax = 28.4°, θmin = 2.3°
φ and ω scans	h = −10→10
21083 measured reflections	k = −12→12
3008 independent reflections	l = −12→12
1909 reflections with I > 2σ(I)

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters not refined
wR(F2) = 0.173	w = 1/[σ2(Fo2) + (0.0939P)2 + 0.0172P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
3008 reflections	Δρmax = 0.28 e Å−3
161 parameters	Δρmin = −0.28 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.13052 (18)	0.06171 (17)	0.37786 (16)	0.0472 (4)
C2	0.17983 (19)	−0.04861 (19)	0.50781 (18)	0.0573 (4)
H2	0.3002	−0.0812	0.5133	0.069*
C3	−0.04832 (19)	0.10990 (19)	0.37058 (17)	0.0571 (4)
H3	−0.0808	0.1842	0.2832	0.068*
C4	0.26416 (18)	0.13439 (17)	0.24324 (17)	0.0495 (4)
O5	0.22778 (14)	0.22924 (14)	0.12885 (12)	0.0638 (3)
O6	0.43403 (13)	0.08074 (13)	0.26489 (12)	0.0605 (3)
C7	0.56778 (19)	0.15655 (18)	0.15091 (17)	0.0528 (4)
C8	0.58804 (18)	0.30400 (19)	0.15298 (16)	0.0510 (4)
C9	0.72527 (19)	0.37414 (19)	0.04596 (17)	0.0533 (4)
H9	0.74	0.4734	0.0448	0.064*
C10	0.8414 (2)	0.2986 (2)	−0.05965 (17)	0.0563 (4)
C11	0.8181 (2)	0.1522 (2)	−0.0585 (2)	0.0629 (4)
H11	0.8951	0.1007	−0.1287	0.075*
C12	0.6796 (2)	0.0814 (2)	0.04764 (19)	0.0606 (4)
H12	0.6634	−0.0171	0.048	0.073*
O13	0.47003 (14)	0.36676 (15)	0.26266 (13)	0.0671 (4)
C14	0.5024 (3)	0.5069 (3)	0.2795 (2)	0.0772 (5)
H14A	0.4104	0.5401	0.3594	0.116*
H14B	0.5013	0.5901	0.1852	0.116*
H14C	0.6174	0.4852	0.3054	0.116*
C15	0.9940 (3)	0.3774 (3)	−0.1702 (2)	0.0793 (6)
H15A	0.9572	0.4919	−0.1881	0.095*
H15B	1.0958	0.345	−0.1214	0.095*
C16	1.0537 (4)	0.3429 (5)	−0.3182 (3)	0.1076 (12)	0.796 (4)
H16	0.9698	0.3704	−0.379	0.129*	0.796 (4)
C17	1.2197 (6)	0.2748 (5)	−0.3724 (4)	0.0998 (13)	0.796 (4)
H17A	1.3071	0.2457	−0.3147	0.12*	0.796 (4)
H17B	1.2481	0.2565	−0.4679	0.12*	0.796 (4)
C16A	1.1284 (19)	0.308 (2)	−0.2471 (13)	0.1076 (12)	0.204 (4)
H16A	1.2244	0.2457	−0.2032	0.129*	0.204 (4)
C17A	1.131 (2)	0.328 (2)	−0.4139 (18)	0.0998 (13)	0.204 (4)
H17C	1.0342	0.3905	−0.4567	0.12*	0.204 (4)
H17D	1.2291	0.2776	−0.4728	0.12*	0.204 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0432 (7)	0.0501 (8)	0.0454 (7)	−0.0193 (6)	−0.0051 (6)	−0.0048 (6)
C2	0.0388 (7)	0.0652 (9)	0.0570 (9)	−0.0165 (7)	−0.0099 (6)	0.0022 (7)
C3	0.0470 (8)	0.0636 (9)	0.0493 (8)	−0.0173 (7)	−0.0112 (6)	0.0050 (7)
C4	0.0437 (7)	0.0533 (8)	0.0483 (8)	−0.0176 (6)	−0.0061 (6)	−0.0064 (6)
O5	0.0527 (6)	0.0754 (7)	0.0511 (6)	−0.0245 (5)	−0.0099 (5)	0.0068 (5)
O6	0.0411 (5)	0.0664 (7)	0.0572 (6)	−0.0207 (5)	−0.0047 (5)	0.0078 (5)
C7	0.0397 (7)	0.0609 (9)	0.0469 (8)	−0.0186 (6)	−0.0056 (6)	0.0033 (7)
C8	0.0408 (7)	0.0666 (9)	0.0430 (7)	−0.0167 (6)	−0.0059 (6)	−0.0093 (7)
C9	0.0468 (8)	0.0635 (9)	0.0487 (8)	−0.0217 (7)	−0.0058 (6)	−0.0091 (7)
C10	0.0442 (8)	0.0669 (10)	0.0509 (8)	−0.0198 (7)	−0.0012 (6)	−0.0078 (7)
C11	0.0493 (8)	0.0692 (10)	0.0624 (10)	−0.0157 (7)	0.0028 (7)	−0.0169 (8)
C12	0.0504 (8)	0.0576 (9)	0.0676 (10)	−0.0171 (7)	−0.0050 (7)	−0.0102 (8)
O13	0.0565 (7)	0.0899 (9)	0.0554 (7)	−0.0283 (6)	0.0073 (5)	−0.0253 (6)
C14	0.0706 (12)	0.1002 (14)	0.0715 (12)	−0.0233 (10)	−0.0042 (9)	−0.0409 (11)
C15	0.0622 (11)	0.0902 (13)	0.0771 (12)	−0.0381 (9)	0.0212 (9)	−0.0240 (10)
C16	0.104 (2)	0.185 (3)	0.0448 (15)	−0.100 (2)	0.0031 (13)	−0.0068 (17)
C17	0.112 (3)	0.115 (3)	0.074 (2)	−0.060 (2)	0.0317 (19)	−0.041 (2)
C16A	0.104 (2)	0.185 (3)	0.0448 (15)	−0.100 (2)	0.0031 (13)	−0.0068 (17)
C17A	0.112 (3)	0.115 (3)	0.074 (2)	−0.060 (2)	0.0317 (19)	−0.041 (2)

C1—C3	1.379 (2)	C11—H11	0.93
C1—C2	1.385 (2)	C12—H12	0.93
C1—C4	1.4903 (18)	O13—C14	1.421 (2)
C2—C3i	1.3844 (19)	C14—H14A	0.96
C2—H2	0.93	C14—H14B	0.96
C3—C2i	1.3844 (19)	C14—H14C	0.96
C3—H3	0.93	C15—C16A	1.257 (15)
C4—O5	1.1937 (17)	C15—C16	1.461 (4)
C4—O6	1.3512 (17)	C15—H15A	0.97
O6—C7	1.4123 (15)	C15—H15B	0.97
C7—C12	1.360 (2)	C16—C17	1.333 (5)
C7—C8	1.390 (2)	C16—H16	0.93
C8—O13	1.3600 (18)	C17—H17A	0.93
C8—C9	1.3843 (18)	C17—H17B	0.93
C9—C10	1.388 (2)	C16A—C17A	1.53 (2)
C9—H9	0.93	C16A—H16A	0.93
C10—C11	1.378 (2)	C17A—H17C	0.93
C10—C15	1.5154 (19)	C17A—H17D	0.93
C11—C12	1.391 (2)
C3—C1—C2	119.99 (12)	C7—C12—H12	120.1
C3—C1—C4	117.51 (13)	C11—C12—H12	120.1
C2—C1—C4	122.49 (13)	C8—O13—C14	117.13 (12)
C3i—C2—C1	119.41 (14)	O13—C14—H14A	109.5
C3i—C2—H2	120.3	O13—C14—H14B	109.5
C1—C2—H2	120.3	H14A—C14—H14B	109.5
C1—C3—C2i	120.59 (14)	O13—C14—H14C	109.5
C1—C3—H3	119.7	H14A—C14—H14C	109.5
C2i—C3—H3	119.7	H14B—C14—H14C	109.5
O5—C4—O6	123.12 (12)	C16A—C15—C10	124.7 (6)
O5—C4—C1	124.73 (13)	C16—C15—C10	116.08 (18)
O6—C4—C1	112.14 (12)	C16—C15—H15A	108.3
C4—O6—C7	116.11 (11)	C10—C15—H15A	108.3
C12—C7—C8	121.45 (13)	C16—C15—H15B	108.3
C12—C7—O6	120.02 (14)	C10—C15—H15B	108.3
C8—C7—O6	118.43 (14)	H15A—C15—H15B	107.4
O13—C8—C9	125.43 (14)	C17—C16—C15	124.7 (4)
O13—C8—C7	116.30 (12)	C17—C16—H16	117.6
C9—C8—C7	118.27 (14)	C15—C16—H16	117.6
C8—C9—C10	121.04 (15)	C16—C17—H17A	120
C8—C9—H9	119.5	C16—C17—H17B	120
C10—C9—H9	119.5	H17A—C17—H17B	120
C11—C10—C9	119.29 (14)	C15—C16A—C17A	118.7 (15)
C11—C10—C15	121.73 (15)	C15—C16A—H16A	120.7
C9—C10—C15	118.95 (15)	C17A—C16A—H16A	120.7
C10—C11—C12	120.13 (16)	C16A—C17A—H17C	120
C10—C11—H11	119.9	C16A—C17A—H17D	120
C12—C11—H11	119.9	H17C—C17A—H17D	120
C7—C12—C11	119.82 (16)